isocytisoside

Base Information

• Chemical Name: isocytisoside
• CAS No.: 4328-19-2
• Molecular Formula: C22H22O10
• Molecular Weight: 446.411
• Mol file: 4328-19-2.mol

Synonyms:isovitexin 4'-methyl ether;5,7-Dihydroxy-2-(4-methoxy-phenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-chromen-4-one;4'-O-methylisovitexin;isovitexin 3'-methyl ether;isovitexin-4'-methyl ether;4'-methoxy-5,7-dihydroxyflavone 6-D-glucopyranoside;

Chemical Property of isocytisoside

Chemical Property:

• Vapor Pressure: 5.03E-25mmHg at 25°C
• Boiling Point: 771.3°Cat760mmHg
• Flash Point: 271.4°C
• PSA: 170.05000
• Density: 1.583g/cm³
• LogP: 0.39470

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of isocytisoside

There total 5 articles about isocytisoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

2,5,7-Trihydroxy-4'-methoxyflavanon (58124-20-2) + UDP-glucose → 4'-methoxy-5,7-dihydroxyflavone 6-D-glucopyranoside (4328-19-2) + apigenin 4'-methoxy-8-C-β-D-glucopyranoside (2326-34-3)

Guidance literature:

With recombinant Oryza sativa C-glycosyltransferase; In ethanol; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.phytochem.2016.02.013

Reference yield:

sileneside D → 4'-methoxy-5,7-dihydroxyflavone 6-D-glucopyranoside (4328-19-2) + D-glucose (50-99-7)

Guidance literature:

With trifluoroacetic acid; at 120 ℃;

DOI:10.1007/s10600-020-03220-x

Reference yield:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (18065-05-9) → 4'-methoxy-5,7-dihydroxyflavone 6-D-glucopyranoside (4328-19-2) + apigenin 4'-methoxy-8-C-β-D-glucopyranoside (2326-34-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / Reflux

2: potassium hydroxide / pyridine / 1 h / 85 °C / Inert atmosphere

3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran

4: recombinant Oryza sativa C-glycosyltransferase / ethanol / 30 °C / pH 7.5 / Enzymatic reaction

With dmap; palladium 10% on activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; 2: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.phytochem.2016.02.013

upstream raw materials:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

2,5,7-Trihydroxy-4'-methoxyflavanon

Downstream raw materials:

5,7,4'-tri-O-methyl-6-C-β-D-glucopyranosylacacetin

Refernces

• 1、 Hao,Caulfield,Hamilton,Pickett,Midega,Khan,Wang,Hooper. "Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins". . p. 73 - 87. Retrieved 2016/04/06.